Design, synthesis, and preliminary biological evaluation of a novel triazole analogue of ceramide

  • Bioorg Med Chem Lett. 2007 Aug 15;17(16):4584-7. doi: 10.1016/j.bmcl.2007.05.086.
Sanghee Kim  1 ,  Minjae Cho ,  Taeho Lee ,  Sukjin Lee ,  Hye-Young Min ,  Sang Kook Lee
Affiliations
  • 1. College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Republic of Korea. [email protected]
PMID: 17561396 DOI: 10.1016/j.bmcl.2007.05.086
Abstract

The amide bond of ceramide was replaced by the non-hydrolyzable 1,2,3-triazole functionality. Click chemistry was employed for synthesis of the designed analogues. Our preliminary biological evaluation indicated that the amide moiety of ceramide is amenable to bioisosteric substitution with the triazole moiety. Some of the analogues were more potent than C2-ceramide as cytotoxic agents, and the observed cytotoxicity was possibly mediated through the induction of Apoptosis.